There has been some discussion on the forum recently about the, ahem, dated-ness of square toed boots and shoes.

I've been eyeing my black booty collection suspiciously. They are only a couple of years old, and, although they need a little spit and polish, they would easily last me another season.

1, and on the left in photo 3: My Aerosoles dress booties. These are easy to work in, even on 10 hour teaching days. This length is tricky on most people, but it hits me just at the curve in my calf and works with dresses, when worn with dark hosiery. I no longer care for the snipped toe, but there is a seam across the toe, and another making a sort of yoke near my ankle that gives a bit of a Victorian feel that works with my overall style.

2, and on the right in photo 3: Liz Claiborne booties. These have a comfy rubber sole, but they're a little narrow, so I don't wear them 2 days in a row. I don't wear these with skirts, because they are awkward looking at the ankle, but they're a great heel height for pants. NOT comfy enough for, say, a shopping expedition in Chicago.

4. New pointy toed flats (Kenneth Cole Reaction, DSW). I love these pewter flats. I sized up to give me adequate room in the toe box, and added a ball of foot cushion to keep my feet from pushing forward in the shoe. They are a replacement for the metallic flats on the left in #5. I appreciate that the point is not exaggerated. I think they'll work with both pants and dresses/skirts.

I'm leaning toward allowing boot #1 to stay, although I'll replace if my funds hold up and I find a better dress bootie. I wouldn't buy the snipped square toe now, perhaps, but I don't want to throw out shoes that have some redeeming qualities. #2, however, is on probation. I think I could use something more comfortable -- shopping worthy.

What say ye? Any suggestions for a truly comfy black bootie? 1-2 inch heels are best, and my foot runs all little wide. Budget matters -- under $100 is best, but I could go as high as $150 for something exceptional.